Bart gets sent to juvenile hall, where he is dragged into escaping with a female prisonmate.

!! Tropes:

* AwLookTheyReallyDoLoveEachOther: Bart is confused by Gina as well as annoyed by her constantly-changing attitude towards him, but when he finds out that, unlike him, she doesn't have a family as he had previously thought, he organises a Mexican food feast in her cell at juvenile hall with the rest of his family, something she appreciates.
* BearsAreBadNews: Chief Wiggum gets mauled by a bear, which is arrested at the end of the episode. Cletus even whittled this event before it happened.
* ButtMonkey: Bart in juvenile hall. Every time he tries to find somewhere to go or something to do, he realises he can't go there or do it because he will get beaten up, so he decides to hang out by the fence to the girls' juvie. [[TemptingFate Unfortunately, this gets his uniform sliced up]].
* DoubleStandardAbuseFemaleOnMale: Gina slices up Bart's uniform when they first meet, and punches him numerous times throughout the episode. Averted when, near the end, she attacks Bart one time too many, and, [[RageBreakingPoint having had enough]], he fights back.
* FailedASpotCheck: Bart fails to see Chief Wiggum being mauled by a bear near him as he decides to go back and find Gina.
* {{Foreshadowing}}:
** Cletus demonstrates the ability to foresee events before they happen and whittles them out in little wooden statuettes. One such scene portrays Chief Wiggum [[BearsAreBadNews getting attacked by a bear]]. This later comes true as a FunnyBackgroundEvent.
** After Gina slices up Bart's uniform, she turns her head to look at him as he is walking away.
* GeniusDitz: Cletus. He's a hillbilly and definitely not the sharpest knife in the drawer (he was dumb enough to drink out of a thermometer), but he's a good observer and whittles what he sees, so he's able to help Chief Wiggum in tracking down Bart and Gina. He's also able to whittle the future, [[BearsAreBadNews in particular Chief Wiggum getting mauled by a bear]], which comes true later.
* GroinAttack: When Gina slices up Bart's uniform, she implies she will castrate him by saying his "puberty will be very boring" if he comes near the fence again.
* HeelRealization: Gina has one when she and Bart are arrested, and told that Bart will stay in juvenile hall even longer because of her. It inspires her to confess to Lou and Eddie that she was the one behind the escape.
* JerkWithAHeartOfGold: Gina is a vicious and cruel delinquent, and is not only willing to lie to get Bart in trouble, but threaten and attack him a few times. But it turns out her anger is due to having no family. And when she learns what Bart will go through because of her, she confesses to forcing him to make a prison break.
* KnifeNut: Gina, which we see when she's introduced.
* [[ManipulativeBastard Manipulative Bitch]]: Gina claims she can act all sad to make Bart take the blame for their escape. After seeing her act, Bart claims he is screwed.
* MeaningfulName: Gina's surname of Vendetti is a clear pun on "vendetta", which is Italian for "revenge", referring to her vicious and manipulative nature.
* MundaneMadeAwesome: The blacksmith forging the key that is used to unlock Bart and Gina's handcuffs is played out this way.
* NoSell: Bart tries to bribe his way out of punishment by bribing Chief Wiggum with the wedding presents at the start of the episode, but it doesn't work as Chief Wiggum only accepts cash bribes.
* OrphansOrdeal: Poor Gina, when Bart finds her crying and realizes she doesn't have a family.
* PapaWolf: Homer decides to become a guard at the juvenile hall in order to try and protect Bart from being beaten up. It works, but only briefly.
* RageBreakingPoint: Bart [[ButtMonkey goes through a lot in this episode]], but when Gina lashes out at him again after he tries to comfort her when he finds her sobbing because of not having a family, he decides he's had enough and fights back.
* ScrewTheRulesIHaveMoney: When Chief Wiggum arrested Bart, Bart tried to bribe his way out with a gift but Wiggum pointed to his badge, which read "Cash Bribes Only".
** ScrewTheRulesImDoingWhatsRight: After Gina confesses to her part on the escape, Wiggum decides to let Bart go despite him still having two weeks left in his sentence.
* {{Tsundere}}: Gina full stop.